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Volumn 59, Issue 35, 2003, Pages 6771-6784

Application of acyl cyanophosphorane methodology to the synthesis of protease inhibitors: Poststatin, eurystatin, phebestin, probestin and bestatin

Author keywords

Acyl cyanophosphorane; Poststatin; keto amides

Indexed keywords

ACYL CYANOPHOSPHORANE; AMIDE; BESTATIN; EURYSTATIN; PHOSPHORANE DERIVATIVE; POSTSTATIN; PROBESTIN; PROTEINASE INHIBITOR; UNCLASSIFIED DRUG;

EID: 0042158455     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00860-3     Document Type: Article
Times cited : (38)

References (41)
  • 28
    • 85031144182 scopus 로고    scopus 로고
    • The earlier general route to α-keto amides from carboxylic acids followed the sequence shown below
    • The earlier general route to α-keto amides from carboxylic acids followed the sequence shown below.
  • 30
    • 85031131067 scopus 로고    scopus 로고
    • 9a formed most probably by the intramolecular addition of the free amino group to the nitrile (see Section 3.1.2)
    • A side product in the deprotection of 8 was shown to be the pyrrolidin-3-one 9a formed most probably by the intramolecular addition of the free amino group to the nitrile (see Section 3.1.2).
  • 31
    • 85031133884 scopus 로고    scopus 로고
    • The synthetic poststatin was identical in all respects to a sample kindly provided by Dr Y. Muraoka
    • The synthetic poststatin was identical in all respects to a sample kindly provided by Dr Y. Muraoka.
  • 36
    • 85031133811 scopus 로고    scopus 로고
    • was prepared from 4-methyl-1-pentanol by oxidation to the corresponding aldehyde. Wittig olefination with (tert-butoxycarbonylmethylene)triphenylphosphorane afforded tert-butyl-(E)-6-methyl-2-heptenoate as a 95:5 mixture of geometric isomers. Deprotection with TFA followed by fractional distillation gave the isomerically pure (E)-acid
    • (E)-6-Methyl-2-heptenoic acid ( 31 ) was prepared from 4-methyl-1-pentanol by oxidation to the corresponding aldehyde. Wittig olefination with (tert-butoxycarbonylmethylene)triphenylphosphorane afforded tert-butyl-(E)-6-methyl-2-heptenoate as a 95:5 mixture of geometric isomers. Deprotection with TFA followed by fractional distillation gave the isomerically pure (E)-acid 31.
  • 37
    • 85031137772 scopus 로고    scopus 로고
    • 13C NMR spectra of all intermediates. Additional evidence was obtained from a 1:1 mixture of 22 and its alanine epimer prepared by equilibration with triethylamine. Cyclization, according to the protocol shown in Scheme 6, furnished 29 and its alanine epimer in a ratio of 1:1. This control experiment demonstrated unambiguously that the stereochemistry of 29 was intact
    • 13C NMR spectra of all intermediates. Additional evidence was obtained from a 1:1 mixture of 22 and its alanine epimer prepared by equilibration with triethylamine. Cyclization, according to the protocol shown in Scheme 6, furnished 29 and its alanine epimer in a ratio of 1:1. This control experiment demonstrated unambiguously that the stereochemistry of 29 was intact.
  • 40
    • 85031135128 scopus 로고    scopus 로고
    • We thank Dr Takaaki, Institute of Microbial Chemistry, Tokyo for samples of phebestin and probestin
    • We thank Dr Takaaki, Institute of Microbial Chemistry, Tokyo for samples of phebestin and probestin.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.